heyitsbluejay
While there appears to be some truth to what you said, let me explain why its only an illusion.
1st - Getting a freelance, from home work is already an extreme rarity. Most of the people will work 9-17 in their lives if they are capable enough to get any proper job, or spend most of their days working anywhere that offers them the chance to earn. Most of the jobs are not dream jobs, but necessary ones. As much as it applies to me, it applies to everyone else.
2nd - Jobs that helps you create a passive income are even harder to come by
3rd - If we are talking about contracts, we are talking about money. Childish fears no longer apply. You can either take a leap of faith (or just be normal person and ask already contracted people) that gives you the chance of becoming someone who is realistically unheard off in normal life. When people learns that I live my life with writing (as close I am to reaching the point where I won't be able to do it anymore) they just can't believe me, because of how unusual it is.
4th - If you treat writing as a hobby and do not wish to reach greater heights, why are you considering the contract in the first place? Asking around will let you learn in a flash that to earn, you need to work hard. And while this kind of work is far more pleasant than answering customer calls, it's still a work. You won't get anywhere without daily releases, and after extended period of time, it gets hard to keep them up.